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Good luck finding that island even if you've been there once. Dragonite could just take returning people to Kanto shores, even if they trusted them originally. It is not a reach to assume that Ash and Go looked harmless because they're kids, either. The island is certainly protected, but...

You might want to change your name. Also, this is clearly a very different Dragonite and I don't remember Iris' one accomplishing much. I'm pretty sure that the only tracks from the games are the wild Pokemon and trainer battle themes. Even the Raid theme is original.

The Leon vs. Lance battle is likely going to encourage Ash to train his own Dragonite... and also Charizard.